Efficient conjugation and preferential DNA binding of oligonucleotides containing 2′-O-(2-oxoethyl)arabinouridine

Timofei S. Zatsepin, Yulia M. Ivanova, Dmitry A. Stetsenko, Michael J. Gait, Tatiana S. Oretskaya

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Oligodeoxyribonucleotides were synthesized that contain a novel nucleoside, 2′-O-(2-oxoethyl)arabinouridine. Whereas such oligonucleotides showed only a slight reduction in the T M values of their complexes with complementary DNA, a significant destabilization was observed in the case of duplexes formed with RNA. This may be explained by the C 2′-endo conformation of 2′-O-(2,3-dihydroxypropyl)arabinouridine as demonstrated by NMR experiments in D 2O. The modified oligonucleotides were used to synthesize a number of conjugates with dyes, biotin and a N-modified laminin peptide, by hydrazone and oxime formation. We suggest that the 2′-arabinoaldehyde-containing DNA duplexes may be valuable tools for affinity modification of DNA-binding proteins. © 2004 Published by Elsevier Ltd.
    Original languageEnglish
    Pages (from-to)7327-7330
    Number of pages3
    JournalTetrahedron Letters
    Volume45
    Issue number39
    DOIs
    Publication statusPublished - 20 Sept 2004

    Keywords

    • Aldehyde
    • Conjugation
    • Hydrazone
    • Modified oligonucleotides
    • Oxime

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